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Chapter 11: 38E (page 350)

Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:

Short Answer

Expert verified

E1 reaction is a substitution nucleophilic unimolecular reaction. It follows first-order kinetics with respect to the substrate.

In the E1 reaction, the deprotonation of hydrogen occurs leading to the formation of carbocation which forms the alkene.

Step by step solution

01

E1 reaction

E1 reaction is a substitution nucleophilic unimolecular reaction. It follows first-order kinetics with respect to the substrate.

In the E1 reaction, the deprotonation of hydrogen occurs leading to the formation of carbocation which forms the alkene.

02

Trifluoroacetic acid

Trifluoroacetic acidic is used as a reagent for the formation of arginine the reagent is used for the deprotonation of the t-BOC group which is used for the protection of the amine group.

03

Mechanism 

  1. Protonation occurs
  2. Leaving group is eliminated
  3. Removal of proton

Mechanism

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Most popular questions from this chapter

SN2 reactions take place with inversion of configuration, andSN1 reactions take place with racemization. The following substitution reaction, however, occurs with complete retention of configuration. Propose a mechanism.

.

What stereochemistry do you expect for the trisubstituted alkene obtained by E2 elimination of the following alkyl halide on treatment with KOH? (Reddish brown = Br.)

The antipsychotic drug flupentixol is prepared by the following scheme:

(a) What alkyl chloride B reacts with amine A to form C?

(b) Compound C is treated withSOCl2, and the product is allowed to react with magnesium metal to give a Grignard reagent D. What is the structure of D?

(c) We鈥檒l see in Section 19-7 that Grignard reagents add to ketones, such as E, to give tertiary alcohols, such as F. Because of the newly formed chirality center, compound F exists as a pair of enantiomers. Draw both, and assign R,Sconfiguration.

(d) Two stereoisomers of flupentixol are subsequently formed from F, but only one is shown. Draw the other isomer, and identify the type of stereoisomerism.

How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?

(a)

How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?
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